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Shikonin derivative containing fluorine carboxylic acid ester and synthetic method and application thereof

A technology of shikonin carboxylic acid and fluorine-containing carboxylic acid, which is applied to the preparation of carboxylic acid esters, drug combinations, chemical instruments and methods, etc., and can solve problems such as water solubility, toxic and side effects, and restrictions on the possibility of shikonin

Inactive Publication Date: 2012-06-13
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, because it is a completely fat-soluble natural product, problems such as water solubility and side effects will be encountered during application. These drawbacks restrict the possibility of shikonin becoming a drug. How to solve these problems is the key to the drug The primary task

Method used

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  • Shikonin derivative containing fluorine carboxylic acid ester and synthetic method and application thereof
  • Shikonin derivative containing fluorine carboxylic acid ester and synthetic method and application thereof
  • Shikonin derivative containing fluorine carboxylic acid ester and synthetic method and application thereof

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example 1

[0027] Example 1: The synthetic method of formula I class shikonin derivatives

[0028] Dissolve 50mmol of shikonin and 50mmol of the corresponding carboxylic acid in 20mL of anhydrous dichloromethane, and continue to add catalytic amounts of N,N-dicyclohexylcarbodiimide (DCC) and 4-Dimethylaminopyridine (DMAP), followed by TLC detection to generate corresponding ester derivatives. Add an appropriate amount of silica gel to concentrate the solvent under reduced pressure, and perform column chromatography with ethyl acetate:petroleum ether=1:4 to obtain the corresponding shikonin carboxylate derivatives.

[0029] The reaction takes 2,2-difluoroacetic acid as an example:

[0030]

[0031] Compound 1

[0032] Compounds 2-8 can be obtained in the same way.

[0033]

[0034] Compound 1 Compound 2 Compound 3 Compound 4

[0035]

[0036] Compound 5 Compound 6 Compound 7 Compound 8

[0037] The physicochemical data of the corresponding compounds are as follows:

[0038]...

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Abstract

The invention belongs to the technical field of chemical pharmacy, particularly relates to preparation of a derivative containing fluorine carboxylic acid ester and application of the derivative in tumor inhibition. The ester derivative is obtained by intriducing fluorocarboxylic acid in shikonin framework molecules through a synthetic method. An in-vitro antitumor activity study shows that the derivative containing the fluorocarboxylic acid has strong inhibition activity to tumor cell lines.

Description

1: Technical field [0001] The invention belongs to the technical field of chemical pharmacy, and in particular relates to the preparation of a class of fluorine-containing carboxylic acid ester derivatives and their application in tumor suppression. Two: background technology [0002] Shicaoning has broad-spectrum activity, and because of its obvious bactericidal activity, it was also used in daily necessities in the early days. Numerous studies in recent years have shown that it is an anti-tumor functional molecule with great potential. However, because it is a completely fat-soluble natural product, problems such as water solubility and side effects will be encountered during application. These drawbacks restrict the possibility of shikonin becoming a drug. How to solve these problems is the key to the drug The primary task. [0003] In order to obtain high-efficiency shikonin derivatives, many research groups have carried out the preparation and activity research of cor...

Claims

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Application Information

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IPC IPC(8): C07C69/63C07C67/08A61K31/222A61P35/00
Inventor 杨永华王小明浩日沁巴图刘洪昌戚金亮林红艳石靖孔文尧
Owner NANJING UNIV
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